6-Deoxy-6-fluoro galactofuranosides regioselective glycosylation, unexpected reactivity, and anti-leishmanial activity

Jeane Vaugenot (1) , Abderrafek El Harras (1) , Olivier Tasseau (1) , Rémi Marchal (1) , Laurent Legentil (1) , Boris Le Guennic (1) , Thierry Benvegnu (1) , Vincent Ferrières (1)

1 ISCR - Institut des Sciences Chimiques de Rennes

Selective glycosylation of the C-6 fluorinated galactofuranosyl acceptor 2 was studied with four galactofuranosyl donors. It was highlighted that this electron-withdrawing atom strongly impacted the behavior of the acceptor, thus leading to unprecedented glycosylation pathways. Competition between expected glycosylation of 2, ring expansion of this acceptor and furanosylation, and intermolecular aglycon transfer was observed. Further investigation of the fluorinated synthetic compounds showed that the presence of fluorine atom contributed to increase the inhibition of the growth of Leishmania tarentolae, a non-pathogenic strain of Leishmania.

Domains: Chemical Sciences; Chemical Sciences; Organic chemistry

Jeane Vaugenot, Abderrafek El Harras, Olivier Tasseau, Rémi Marchal, Laurent Legentil, et al.. 6-Deoxy-6-fluoro galactofuranosides regioselective glycosylation, unexpected reactivity, and anti-leishmanial activity. Organic & Biomolecular Chemistry, 2020, 18 (7), pp.1462-1475. ⟨10.1039/c9ob02596k⟩. ⟨hal-02472159⟩